The business world is shifting in a new direction.
What used to be standard—having a dedicated, full-time C-suite assistant—is becoming more flexible and fractional.
This change took off when Tim Ferriss published “The 4-Hour Work Week” in 2007.
His bold idea? That you could run a million-dollar business with a $5-per-hour virtual assistant from overseas!
His concept changed everything in the virtual assistance industry, especially in the United States.
Companies jumped on board, racing to offer the lowest possible rates while calling themselves “virtual executive assistant” services.
But here’s the question: is this race to the bottom really serving executives who need top-tier support? Let’s find out!
What is an Outsourced Executive Assistant?
Nowadays, you have several options for administrative support.
At one end of the spectrum, you’ll find overseas virtual assistants charging as little as $5 per hour.
In the middle, there are US-based virtual assistants charging $40-60 per hour but often juggling many clients at once.
And at the top end, there’s the traditional full-time executive assistant, commanding salaries of $75,000 to $150,000+ annually.
But there’s a sweet spot between these options: the outsourced executive assistant.
An outsourced executive assistant is an experienced professional who provides high-level support to executives, entrepreneurs, and business owners while working remotely rather than as an in-house employee.
These seasoned professionals have chosen to work with a select few clients rather than a single employer. They bring their high-level experience to multiple businesses while maintaining the personal touch of a dedicated assistant.
What makes them different?
Unlike traditional virtual assistants who might handle basic tasks for 8-10 clients, outsourced executive assistants typically maintain a lower client-to-assistant ratio (3:1 or lower) and offer comprehensive support across five key areas:
- Core administrative and scheduling functions
- Business partnership and strategic support
- Project management
- Chief of staff duties
- Personal assistance
They’ve often chosen this path because it allows them to leverage their expertise across multiple businesses, maintain work-life balance, and provide high-quality service to each client.
This model works particularly well for small and medium-sized businesses where CEOs need high-level support but may not require (or be ready for) a full-time assistant.
Want to see if an outsourced executive assistant is right for you?
At ProAssisting, we offer elite support starting at $3,000 per month—that’s 50-80% less than hiring in-house.
Our ProAssistants bring 5+ years of experience from globally recognized brands and work with a maximum of 1-2-3 clients to ensure dedicated attention.
Schedule a free consultation to learn how a ProAssistant can transform your workday!
Benefits of Outsourced Executive Assistant Services
Let’s see why executives turn to outsourced assistance and how it can help you:
Cost-Effective Solution
When you hire a full-time executive assistant in a major metropolitan area, you’re looking at a six-figure investment when you factor in salary, benefits, and overhead.
An outsourced executive assistant can save you many of these costs.
You’ll only pay for the resources you need, without worrying about benefits, equipment, or training expenses.
You get top-tier support without the full-time price tag:
- No hidden costs for healthcare or retirement benefits
- Zero expenses for office space or equipment
- Pay only for actual work hours or fractional resources, not downtime
- Skip costly recruitment and training processes
Flexibility That Works for You
One of the biggest advantages of working with an outsourced assistant is the flexibility you get.
Need more support during busy seasons?
Want to scale back during slower periods?
No problem.
- Adjust your support hours monthly based on your needs
- Avoid complicated HR processes when changing support levels
- Access backup support when your primary assistant is away
- Change or end the arrangement without severance complications
High-Level Experience at Your Fingertips
Your outsourced executive assistant isn’t just any assistant—they’re a seasoned professional who has chosen to work with multiple clients instead of a single employer.
These professionals typically bring years of experience working with C-suite executives and understand the nuances of high-level business operations.
With an outsourced EA, you get someone who can think strategically, solve complex problems, and maintain the highest level of discretion.
They’ve likely worked across various industries and bring best practices from each experience to support your business.
Free Up Time to Focus on Core Business Functions
According to Prialto’s 2024 Productivity Report, 42% of executives cite administrative tasks and busy work as a major productivity blocker, up from 38% in 2022.
Outsourced executive assistants help reclaim this lost time by managing:
- Calendar and email management
- Travel arrangements and logistics
- Document preparation and organization
- Meeting coordination and follow-up
- Project management and tracking
Continuous Growth and Innovation
Because outsourced executive assistants work with multiple executives, they’re constantly learning new tools, strategies, and efficiency methods.
This means you benefit from their diverse experience and upgraded skill set.
They bring fresh perspectives and innovative solutions they’ve learned from working across different organizations and industries.
The fractional model attracts highly motivated professionals invested in continuous improvement and maintaining high service standards.
Steps to Maximize the Value of Admin Outsourcing
Getting the most value from your outsourced executive assistant starts with honest self-reflection and smart planning.
Let’s break down the steps that will help you create a successful working relationship that improves over time:
Step 1: Be Brutally Honest With Yourself
Before you get into it, take a good look at your typical workday and ask yourself some tough questions:
What tasks do you consistently put off?
Which responsibilities do you struggle with?
What work do you tell yourself “I can do it faster myself” about—even though it’s eating up your valuable time?
Key tasks to watch for:
- Emails that drain your energy and attention
- Meetings that always seem to need rescheduling
- Regular reports you procrastinate on creating
- Travel arrangements that stress you out
- Personal tasks that keep falling through the cracks
Step 2: Plan for Long-Term
Look carefully at your balance sheet before making this commitment.
While most services offer month-to-month contracts, the real value of an executive assistant typically kicks in after three solid months of working together.
Can your business sustain this investment during the learning period?
Your financial and operational planning should cover:
- Monthly budget allocation for assistant services
- Expected return on investment timeline
- Cash flow considerations for at least a 3-month commitment
- Which tasks will have immediate ROI versus long-term value
- Your comfort level with delegating different types of tasks
This is an investment in your productivity. Think of those first three months as building an asset for your business rather than just an expense.
Step 3: Create Clear Communication Channels
You need to establish clear guidelines from day one while staying flexible enough to adapt as the relationship grows.
Essential elements to define:
- Expected response times for different types of requests
- Regular check-in meeting schedule and format
- Preferred communication methods for various situations
- Initial priorities and how they might change
Step 4: Build Trust Systematically
The first 90 days are your foundation-building period.
Remember, even the most experienced assistant needs time to learn your specific needs and preferences.
Fight the urge to do everything yourself—invest time upfront to save hours later.
Here’s what successful partnerships do:
- Start with lower-stakes tasks to build confidence initially
- Schedule weekly feedback sessions to fine-tune processes
- Document preferences and successful workflows
- Celebrate small wins and learn from any missteps
Step 5: Set Up Your Digital Infrastructure
You’ll need some basic tools to work effectively with your remote assistant. Start with the essentials and build from there.
Must-have tools include:
- A reliable video conferencing platform (Meet, Zoom, Teams, etc.)
- A secure password management system
- A shared task-tracking solution
- Cloud storage for collaborative work
Don’t overhaul your entire workflow overnight.
Start with these fundamentals and let your system adapt naturally as you and your assistant find your rhythm together.
How to Hire an Executive Assistant
Partner with an experienced remote executive assistant you can depend on so you can free up your time to focus on strategic growth and super-high-level things only!
At ProAssisting, our executive assistants have supported executives and non-executive board members at some of the world’s top brands (Walmart, BCG, JPMorgan, Airbnb, Target, Oracle, etc.).
Here’s how we find and select only the most qualified professionals to serve our clients:
Our Rigorous Selection Process
We start by carefully reviewing each candidate’s complete professional story.
This means matching LinkedIn profiles against resumes to ensure consistency and authenticity.
We’re looking for clear career progression and thoughtful presentation—even small details like a customized LinkedIn background image tell us about a candidate’s attention to detail and professional pride.
Our standards are exceptionally high—we accept less than 5% of applicants, ensuring only the most qualified professionals join our team.
When evaluating potential ProAssistants, we look beyond just the bullet points on a resume.
We dig deep into:
- How they present their experience and achievements
- The flow and clarity of their written communication
- Their ability to tell compelling stories about past successes
- Evidence of strong work ethic and problem-solving abilities
The Human Element
Technical skills matter, but we know that soft skills make the difference between a good assistant and a great one.
During our interview process, we pay close attention to:
- How candidates would represent you to important clients (or stakeholders)
- Their tone of voice and communication style
- The way they handle challenging scenarios
- Their ability to build trust and rapport
Building Trust Through Experience
We believe in starting relationships with clear expectations and open communication.
Each ProAssistant begins with straightforward tasks (like calendar management and travel arrangements) before progressing to more complex responsibilities (such as representing you in meetings or managing major projects like home renovation or office relocation).
This stepped approach allows both you and your ProAssistant to build confidence and trust organically.
While we do check references, we put more weight on our direct interactions and assessment of each candidate’s capabilities and character.
A Partnership Built for Success
Our goal is to match you with someone who not only meets your practical needs but also fits your working style and company culture.
We understand that letting someone new into your business life takes trust, which is why we’re so selective about who becomes a ProAssistant.
What sets us apart is our commitment to fair compensation—we pass 80% of your monthly retainer directly to your ProAssistant, a significantly higher percentage than other businesses in our space.
Because ProAssistants are treated well and compensated accordingly for their high level of expertise, we attract and retain top talent.
This means your ProAssistant will likely be by your side for as long as you need them, providing consistent, high-quality support.
Ready to find your perfect executive assistant match?
Let’s discuss how we can support your success!
Common Hiring Challenges and How to Overcome Them
Nowadays, when you post a job for an executive assistant, you’re going to get flooded with 200, 300, or even 500 applications.
This volume creates unique challenges in finding the right fit.
Here’s what you’re likely to face and how to handle it:
- Screening Overload: Looking through hundreds of applications can feel impossible. There are AI tools that exist for screening, but they often miss the human element that’s crucial for this personal role. Instead, develop a quick 5-second screening system focusing on key experience markers and presentation quality.
- Remote vs. In-Office Expectations: Many C-suite executives still insist, “I want Tom in Office Hall full-time, all the time,” but this mindset needs updating. If your assistant can manage your calendar, handle communications, and coordinate meetings effectively from their laptop or phone, consider giving them location flexibility. Remember, you’re hiring a high-level partner, not just a task manager.
- Rigid Requirements vs. Potential: You might find a candidate who clicks perfectly with your working style but doesn’t tick every box on your checklist. Be open to flexibility here—sometimes, the right personality fit and strong core skills are more valuable than meeting every technical requirement.
- Volume of Applications: When you’re drowning in hundreds of applications, you need a system. Look for these immediate red flags:
- Poorly formatted resumes or obvious template use
- Generic cover letters without personalization
- Lack of relevant executive support experience
- Mismatched LinkedIn profiles and resumes
- Schedule Alignment: If you constantly travel or work across time zones, don’t limit yourself to candidates in your location. A great assistant in New York can effectively support you while you’re in California—it’s about results, not physical presence.
Also, expect to pay a bit more than hiring a virtual assistant. These are two different roles.
While both provide remote support, executive assistants vs. virtual assistants have fundamental differences in experience level, scope of work, and ability to handle complex business responsibilities.
Frequently Asked Questions (FAQs)
Here are the most common questions executives ask about outsourced assistant services.
What is the Cost of an Executive Assistant for Hire?
Contract executive assistants (often called “fractional” assistants because they split their time between clients) typically charge between $35 and $150 per hour.
This wide range reflects different experience levels and service models.
Contract workers usually double their base rate to cover their own benefits, taxes, and business expenses—that’s just the nature of independent contracting.
However, we at ProAssisting take a different approach.
Instead of charging by the hour, we offer monthly retainer packages based on the resources of a top-level executive assistant.
This model often works better for both clients and assistants, ensuring you get consistent support without watching the clock.
Check out our ProAssistant pricing plan for elite executive support if you want a predictable monthly investment.
Which Executive Assistant Companies Offer the Best Service?
When evaluating executive assistant companies, you need to ask two key questions:
How are the assistants compensated, and what happens to unused hours? These answers say a lot about a company’s values and service quality.
ProAssisting stands out by passing 80% of monthly retainers directly to our hand-picked assistants and maintaining a strict 3:1 client ratio.
We also ensure that assistants are paid for all contracted hours, whether used or not, a practice that helps us retain top talent.
Other notable companies in the space include Boldly, which uses a W2 employee model, and Double, which focuses on tech industry support.
Their business models and compensation structures differ significantly from ProAssisting’s entrepreneurial approach.
Remember, the best service often comes from companies that prioritize fair compensation and reasonable workloads for their assistants, as this directly impacts the quality of support you’ll receive.
Can Outsourced Assistants Handle Confidential Tasks?
Yes, professional outsourced executive assistants routinely handle confidential information.
They:
- Sign comprehensive NDAs
- Follow strict security protocols
- Maintain professional discretion
- Have experience with sensitive business information
Conclusion
Finding the right executive support can transform your entire approach to business growth.
The real value comes from finding a partner who can truly improve your work and free you to focus on high-impact activities.
This is where ProAssisting stands apart.
Our ProAssistants are your strategic partners who can represent you in meetings, provide a sounding board for new ideas, and even oversee your personal staff.
They bring a hospitality mindset and a deep understanding of business operations to every interaction.
ProAssistants:
- Respond to communications within an hour or less during business hours.
- Provide after-hours support when you’re traveling.
- Can handle upwards of 95% of what an in-person assistant would do—all while working remotely.
Schedule a 30-minute call with our Co-founder, Ethan Bull, to discover how a dedicated ProAssistant can start impacting your life from day one!
